7-methyl-2,3-dihydro-1H-pyrrolo[2,1-b]quinazolin-9-one | 60811-38-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 7-methyl-2,3-dihydro-1H-pyrrolo[2,1-b]quinazolin-9-one
• 英文别名: 2-methyl-6,7,8,9-tetrahydropyrrolo[2,1-b]quinazolin-11-one；7-methyl-2,3-dihydropyrrolo[2,1-b]quinazolin-9(1H)-one
• CAS: 60811-38-3
• 化学式: C₁₂H₁₂N₂O
• 分子量: 200.24
• InChiKey: WGMDMAZNZCEADV-UHFFFAOYSA-N

物化性质

• 熔点：
  110 °C
• 沸点：
  374.5±35.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  32.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  7-methyl-2,3-dihydro-1H-pyrrolo[2,1-b]quinazolin-9-one 在 sodium tetrahydroborate 、 三乙胺 作用下， 以 乙醇 、 苯 为溶剂， 生成 Methyl 7-methyl-9-oxo-1,2,3,3a-tetrahydropyrrolo[2,1-b]quinazoline-4-carboxylate
  参考文献：
  名称：

  Synthesis, methylation, and acylation of 1,2-dihydrodeoxyvasicinones and their homologs

  摘要：

  DOI：

  10.1007/bf00601291
• 作为产物：
  描述：

  2-azido-5-methylbenzoic acid 在 三甲基氯硅烷 、 氯化亚砜 、 三乙胺 、 sodium iodide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 乙腈 、 苯 为溶剂， 反应 7.25h， 生成 7-methyl-2,3-dihydro-1H-pyrrolo[2,1-b]quinazolin-9-one
  参考文献：
  名称：

  Chemoenzymatic Synthesis of Pyrrolo[2,1-b]quinazolinones:  Lipase-Catalyzed Resolution of Vasicinone

  摘要：

  A facile synthesis of bronchodilatory pyrrolo [2,1-b] quinazoline alkaloids by azidoreductive cyclization strategy employing TMSCl-NaI and bakers' yeast is described. Both the chemical and enzymatic methods are mild and take place at room temperature in good yields. Further, synthesis and resolution of vasicinone has been carried out by employing different lipases. It has been observed that lipase PS provides acetate of (S)-vasicinone in 98% ee.

  DOI：

  10.1021/jo0011484

文献信息

• Mild and efficient reduction of azides to amines: synthesis of fused [2,1-b]quinazolinones
  作者：Ahmed Kamal、K.Venkata Ramana、Hari Babu Ankati、A.Venkata Ramana

  DOI：10.1016/s0040-4039(02)01454-5

  日期：2002.9

  FeCl3/NaI has been employed for an efficient reduction of a variety of azides. This method is selective in the presence of a nitro functionality and has been extended for the synthesis of fused [2,1-b]quinazolinone ring systems such as deoxyvasicinone.

  FeCl 3 / NaI已用于有效还原各种叠氮化物。该方法在硝基官能团存在的情况下是选择性的，并且已经扩展为合成稠合的[ 2,1- b ]喹唑啉酮环系统，例如脱氧维辛酮。
• [EN] TRICYCLIC GYRASE INHIBITORS FOR USE AS ANTIBACTERIAL AGENTS<br/>[FR] INHIBITEURS TRICYCLIQUES DE GYRASE UTILISABLES COMME AGENTS ANTIBACTÉRIENS
  申请人：TRIUS THERAPEUTICS INC

  公开号：WO2014043272A1

  公开（公告）日：2014-03-20

  Disclosed herein are compounds having the structure of Formula I and pharmaceutically suitable salts, esters, and prodrugs thereof that are useful as antibacterially effective tricyclic gyrase inhibitors. In addition, species of tricyclic gyrase inhibitors compounds are also disclosed herein. Related pharmaceutical compositions, uses and methods of making the compounds are also contemplated.

  本文披露了具有化学式I结构的化合物及其药用盐、酯和前药，这些化合物可用作抗菌有效的三环酶抑制剂。此外，本文还披露了三环酶抑制剂化合物的种属。还考虑了相关的药用组合物、用途和制备这些化合物的方法。
• One-Pot Microwave-Assisted Selective Azido Reduction/Tandem Cyclization in Condensed and Solid Phase with Nickel Boride
  作者：Ahmed Kamal、Leonardo Silva Santos、Nagula Shankaraiah、Nagula Markandeya、Marlene Espinoza-Moraga、Claudia Arancibia

  DOI：10.1055/s-0029-1216831

  日期：2009.7

  inexpensive method using microwave-assisted irradiation with Ni2B for the syntheses of aromatic amines, pyrrolobenzodiazepines as well as pyrroloquinazolinones was developed. This protocol was applied in the tandem resin-cleavage, azido reduction, and cyclization of compounds 3 and 5 that afforded substituted pyrrolo[2,1-c][1,4]benzodiazepines 4 and 6 in a one-pot manner. The microwave-assisted irradiation

  开发了一种高效且廉价的方法，该方法使用微波辅助的Ni 2 B辐射来合成芳族胺，吡咯并苯并二氮杂pine以及吡咯并喹唑啉酮。该方案适用于串联式树脂裂解，叠氮基还原和化合物3和5的环化反应，这些化合物以一锅方式提供取代的吡咯并[2,1- c ] [1,4]苯并二氮杂卓4和6。与常规的热反应相比，微波辅助的辐射反应以非常短的反应时间提高了产率。 吡咯并[2,1- c ] [1,4]苯并二氮杂卓-吡咯并喹唑啉酮-叠氮还原环化-硼化镍-微波辐射
• On the Synthesis and Reactivity of 2,3-Dihydropyrrolo[1,2-a]quinazolin-5(1H)-ones
  作者：Charlotte Sutherell、Steven Ley

  DOI：10.1055/s-0035-1562792

  日期：——

  3-dihydropyrrolo[1,2-a]quinazolin-5(1H)-one is reported. The applicability of this method to analogue synthesis and the synthesis of related natural products is explored. Finally, reactivity of the scaffold to a variety of electrophilic reagents, generating products stereoselectively, is reported. An improved, scalable synthetic route to the quinazolinone natural product 2,3-dihydropyrrolo[1,2-a]quinazolin-5(1H)-one

  尊重并祝福我们的朋友对他的70之际迪特·恩德斯专用个生日 抽象的 报道了一种改进的，可扩展的合成路线，该路线合成了喹唑啉酮天然产物2，3-二氢吡咯并[1,2 - a ]喹唑啉-5（1 H）-one。探索了该方法在类似物合成和相关天然产物合成中的适用性。最后，报道了支架对多种亲电试剂的反应性，立体选择性地产生产物。 报道了一种改进的，可扩展的合成路线，该路线合成了喹唑啉酮天然产物2，3-二氢吡咯并[1,2 - a ]喹唑啉-5（1 H）-one。探索了该方法在类似物合成和相关天然产物合成中的适用性。最后，报道了支架对多种亲电试剂的反应性，立体选择性地产生产物。
• TRICYCLIC GYRASE INHIBITORS
  申请人：Bensen Daniel

  公开号：US20120238751A1

  公开（公告）日：2012-09-20

  Disclosed herein are compounds having the structure of Formula I and pharmaceutically suitable salts, esters, and prodrugs thereof that are useful as antibacterially effective tricyclic gyrase inhibitors. Related pharmaceutical compositions, uses and methods of making the compounds are also contemplated.

  本文披露了具有式I结构的化合物，以及作为抗菌有效的三环酶抑制剂的药用盐、酯和前药，相关的药物组合物、用途和制备该化合物的方法也在考虑之中。